2,5-bis[(4-hydroxyphenyl)ethynyl]-3,4-dicyanothiophene | 222639-34-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,5-bis[(4-hydroxyphenyl)ethynyl]-3,4-dicyanothiophene
• 英文别名: 2,5-bis(4-hydroxyphenylethynyl)-3,4-dicyanothiophene；2,5-Bis[2-(4-hydroxyphenyl)ethynyl]thiophene-3,4-dicarbonitrile；2,5-bis[2-(4-hydroxyphenyl)ethynyl]thiophene-3,4-dicarbonitrile
• CAS: 222639-34-1
• 化学式: C₂₂H₁₀N₂O₂S
• 分子量: 366.4
• InChiKey: GDYYANCPGRQTCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-Didecyloxybenzoic acid 、 2,5-bis[(4-hydroxyphenyl)ethynyl]-3,4-dicyanothiophene 在 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,5-bis[4-(3,4-didecyloxyphenylcarbonyloxy)phenylethynyl]-3,4-dicyanothiophene
  参考文献：
  名称：

  The Interplay of Bent-Shape, Lateral Dipole and Chirality in Thiophene Based Di-, Tri-, and Tetracatenar Liquid Crystals

  摘要：

  A range of mesogenic molecules varying in both bend angle and strength of lateral dipole were synthesized, and their phase behavior was characterized by polarizing microscopy, thermal analysis, X-ray diffraction, and electrooptical measurements. We find the general destabilization of the liquid crystallinity caused by strong lateral dipolar groups and the bent molecular shape are off-set in mesomorphic tetracatenars, which display stable nematic, smectic, columnar, and cubic mesophases. The broad mesomorphism of the tetracatenars containing lateral dipoles and their incompatibility with chiral induction are explained by considering that loosely correlated dimers exist within the mesophases. Chiral mesophases of derivatives with strong lateral dipoles were achieved by attaching fewer or different side chains to each end of the mesogen.

  DOI：

  10.1021/ja0268027
• 作为产物：
  描述：

  2,5-bis[(4-benzyloxyphenyl)ethynyl]-3,4-dicyanothiophene 在 B-溴代邻苯二氧硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以91%的产率得到2,5-bis[(4-hydroxyphenyl)ethynyl]-3,4-dicyanothiophene
  参考文献：
  名称：

  The Interplay of Bent-Shape, Lateral Dipole and Chirality in Thiophene Based Di-, Tri-, and Tetracatenar Liquid Crystals

  摘要：

  A range of mesogenic molecules varying in both bend angle and strength of lateral dipole were synthesized, and their phase behavior was characterized by polarizing microscopy, thermal analysis, X-ray diffraction, and electrooptical measurements. We find the general destabilization of the liquid crystallinity caused by strong lateral dipolar groups and the bent molecular shape are off-set in mesomorphic tetracatenars, which display stable nematic, smectic, columnar, and cubic mesophases. The broad mesomorphism of the tetracatenars containing lateral dipoles and their incompatibility with chiral induction are explained by considering that loosely correlated dimers exist within the mesophases. Chiral mesophases of derivatives with strong lateral dipoles were achieved by attaching fewer or different side chains to each end of the mesogen.

  DOI：

  10.1021/ja0268027

文献信息

• Exciton Coupling and Dipolar Correlations in a Columnar Liquid Crystal:  Photophysics of a Bent-Rod Hexacatenar Mesogen
  作者：Igor A. Levitsky、Keiki Kishikawa、S. Holger Eichhorn、Timothy M. Swager

  DOI：10.1021/ja993947d

  日期：2000.3.1

  A novel bent-rod hexacatenar liquid crystal is reported that displays a hexagonal columnar (Col(h)) phase. The organization of conjugated hexacatenar mesogens in the columnar phase is of interest for their anisotropic electronic properties. The emissive nature of the mesogens varies over the temperature range of the Col(h) phase and the spectral shifts were analyzed in terms of an exciton-coupling model. The variation of the emission band in this phase is consistent with varying degrees of rotational disorder between the mesogens. The bent-rod shape and highly dipolar nature of the liquid crystal core (mesogen) promotes (as suggested by computation, X-ray diffraction, and photophysical studies) a high degree of antiparallel intermolecular correlations between nearest neighbors. The antiparallel organization is novel and differs from structures previously identified in other polycatenars. These studies illustrate the utility of the exciton-caupling model to probe the nature and degree of intermolecular correlations in highly dipolar liquid crystals.
• The Interplay of Bent-Shape, Lateral Dipole and Chirality in Thiophene Based Di-, Tri-, and Tetracatenar Liquid Crystals
  作者：S. Holger Eichhorn、Alexander J. Paraskos、Keiki Kishikawa、Timothy M. Swager

  DOI：10.1021/ja0268027

  日期：2002.10.1

  A range of mesogenic molecules varying in both bend angle and strength of lateral dipole were synthesized, and their phase behavior was characterized by polarizing microscopy, thermal analysis, X-ray diffraction, and electrooptical measurements. We find the general destabilization of the liquid crystallinity caused by strong lateral dipolar groups and the bent molecular shape are off-set in mesomorphic tetracatenars, which display stable nematic, smectic, columnar, and cubic mesophases. The broad mesomorphism of the tetracatenars containing lateral dipoles and their incompatibility with chiral induction are explained by considering that loosely correlated dimers exist within the mesophases. Chiral mesophases of derivatives with strong lateral dipoles were achieved by attaching fewer or different side chains to each end of the mesogen.